US4440570A - Process for purifying and recovering contaminated catalyst solution obtained in the carbonylation of methyl acetate and/or dimethylether - Google Patents
Process for purifying and recovering contaminated catalyst solution obtained in the carbonylation of methyl acetate and/or dimethylether Download PDFInfo
- Publication number
- US4440570A US4440570A US06/402,961 US40296182A US4440570A US 4440570 A US4440570 A US 4440570A US 40296182 A US40296182 A US 40296182A US 4440570 A US4440570 A US 4440570A
- Authority
- US
- United States
- Prior art keywords
- organic
- water
- catalyst solution
- noble metal
- carbonyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/40—Regeneration or reactivation
- B01J31/4015—Regeneration or reactivation of catalysts containing metals
- B01J31/4023—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper
- B01J31/4038—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper containing noble metals
- B01J31/4046—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper containing noble metals containing rhodium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0239—Quaternary ammonium compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0255—Phosphorus containing compounds
- B01J31/0267—Phosphines or phosphonium compounds, i.e. phosphorus bonded to at least one carbon atom, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, the other atoms bonded to phosphorus being either carbon or hydrogen
- B01J31/0268—Phosphonium compounds, i.e. phosphine with an additional hydrogen or carbon atom bonded to phosphorous so as to result in a formal positive charge on phosphorous
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/20—Carbonyls
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/40—Regeneration or reactivation
- B01J31/4015—Regeneration or reactivation of catalysts containing metals
- B01J31/4023—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper
- B01J31/4038—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper containing noble metals
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/40—Regeneration or reactivation
- B01J31/4015—Regeneration or reactivation of catalysts containing metals
- B01J31/4092—Regeneration or reactivation of catalysts containing metals involving a stripping step, with stripping gas or solvent
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/573—Separation; Purification; Stabilisation; Use of additives
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/34—Other additions, e.g. Monsanto-type carbonylations, addition to 1,2-C=X or 1,2-C-X triplebonds, additions to 1,4-C=C-C=X or 1,4-C=-C-X triple bonds with X, e.g. O, S, NH/N
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/822—Rhodium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/824—Palladium
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Definitions
- the present invention relates to a process for purifying and recovering a contaminated catalyst solution which is obtained in the carbonylation of methyl acetate and/or dimethylether, the catalyst solution containing carbonyl complexes of noble metals of group VIII of the Periodic System of the elements, quaternary heterocyclic aromatic nitrogen compounds or quaternary organophosphorus compounds as organic promoters, undistillable organic contaminants as well as acetic acid, acetic anhydride and ethylidene diacetate.
- rhodium +++ is first absorbed from the aqueous solution on a cation exchanger and then desorbed by means of hydrochloric acid.
- the hydrochloric acid solution is admixed with tertiary phosphines, treated with CO and, if desired, hydrogen, and rhodium is precipitated as a carbonyl complex.
- the processes described, for example, in DE-OS No. 24 50 965 and 28 36 084 are, however, not of assistance in the purification and recovery of noble metal carbonyl-complexes (Rh, Ir, Pd, Ru) and their promoters from the contaminated catalyst solutions obtained in the carbonylation of methyl acetate or dimethylether.
- the catalyst solution obtained in the carbonylation reaction is composed of 0.1 up to 10 weight % noble metal/carbonyl complex, 40-70 weight % organic promoter, 1-10 weight % undistillable organic contaminants, and 20-40 weight % acetic acid, acetic anhydride and ethylidene diacetate.
- the catalyst solution it is possible for the catalyst solution to contain up to 80 weight % undistillable substances. After removal of volatile constituents by distillation, it is naturally possible to subject the noble metal/carbonyl-complex to oxidative degradation but this would entail the destruction of the entire quantity of organic promoters whereby the beneficial effect which is associated with catalyst work up would be jeopardized from the onset.
- the present invention which enables the adverse effects described hereinabove to be avoided now provides a process wherein distillative operation and, if desired, extractive operation permit catalyst solution which is used and gradually contaminated in the carbonylation of methyl acetate and/or dimethylether to be worked up in such a manner that it is possible for the organic promoters to be used again in the catalyst cycle, undistillable organic contaminants being removed and noble metal being recovered therefrom.
- the present process compares favorably with the work-up methods described heretofore inasmuch as the extractants used for effecting work-up are cycled, pollution of the environment by waste material being substantially avoided. Only those undistillable organic contaminants which are formed during the process and reaction are removed for disposal by incineration, for example, in accordance with pertinent art.
- the present process comprises more particularly: distillatively freeing the catalyst solution from its volatile constituents and water-treating the remaining solid distillation residue, the noble metal/carbonyl-complex being precipitated together with the organic contaminants and the organic promoter becoming dissolved; removing the precipitated and contaminated noble metal/carbonyl-complex by filtration and recovering the noble metal in known manner therefrom; recovering the organic promoter by evaporating the water or extracting it with halogenated hydrocarbons and evaporating these latter.
- reaction mixture coming from the carbonylation reactor is separated distillatively into desirable final products, especially acetic anhydride, acetic acid and/or ethylidene diacetate, and unreacted cycled feed material on the one hand, and into catalyst solution as base material on the other hand.
- a portion of this catalyst solution which becomes gradually contaminated is taken from the catalyst solution cycle and distillatively freed in accordance with this invention, preferably at 100°-120° C. and 1-100 millibars from volatile matter, e.g. acetic acid, acetic anhydride and ethylidene diacetate.
- the noble metals customarily contained in the contaminated catalyst solutions comprise rhodium, iridium, palladium and/or ruthenium which are present as carbonyl complexes e.g. of the formula [CH 3 P(C 4 H 9 ) 3 ] 2 Rh(CO)I 5 or CH 3 P(C 4 H 9 ) 3 Rh(CO) 2 I 2 .
- the catalyst solutions generally contain one or more of the following heterocyclic aromatic nitrogen compounds or organophosphorus compounds:
- N-methylpyridinium iodide N,N-dimethylimidazolium iodide; N-methyl-3-picolinium iodide; N-methyl-2,4-lutidinium iodide; N-methyl-3,4-lutidinium iodide, N-methyl-quinolinium iodide;
- the distillation residue which remains behind should be introduced, preferably with agitation, into water and heated to 70° C., for example.
- the organic promoter portion contained in the distillation residue becomes dissolved in the water phase, whilst the noble metal/carbonyl complex and the undistillable organic contaminants formed during the reaction remain undissolved. Residue insoluble in the water phase is filtered off and should be delivered to a refinery for separation of the organic contaminants and recovery of the pure noble metal as such or as compound, in known fashion.
- the promoter dissolved in the water phase is recovered in the form of pure material, after evaporation of the water, and used again in the reaction.
- the organic promoters being selected from quaternary organophosphorus compounds, it is possible for the organic promoter which is dissolved in the water phase to be also extracted with the use of halogenated hydrocarbons. This naturally means an economy of the expenses incurred by the evaporation of water.
- pure organic promoter is obtained which is recycled to the catalyst solution cycle.
- the water raffinate is freed from the dissolved halogenated hydrocarbon by stripping. Next, water phase and halogenated hydrocarbons can be used again. Needless to say, the process of this invention can be carried out continuously or discontinuously.
- tri-n-butylmethylphosphonium iodide tri-n-butylmethylphosphonium iodide as an organic promoter
- acetic anhydride acetic acid
- ethylidene diacetate organic contaminants and freed from distillable materials under reduced pressure of about 2 millibars and at a base temperature of up to 120° C.
- the water phase obtained by filtration was shaken 6 times, each time with 250 ml chloroform, for recovering the organic promoter.
- 156 g tri-n-butylmethylphosphonium iodide corresponding to a yield of 99.8%, was obtained from the chloroform phase.
- P/I-analysis with 9 weight % phosphorus and 36.9 weight % iodine, IR-analysis and melting point indicated that the organic promoter salt recovered was very pure.
- the extracted water phase was freed from dissolved chloroform by stripping and could be used again.
- the chloroform was used in further operations for extracting organic promoter.
- the distillation residue was comminuted and introduced with agitation into 4500 ml water at 20° C. After 30 minutes, the suspension was heated to 60°-70° C. while agitation was continued. After altogether 1.5 hours, the remaining residue was filtered, after-washed with water and dried at 120° C. under 2 millibars. 25 g weighed material was obtained. Analysis indicated that it contained 0.525 g rhodium.
- the water phase originating from the filtration was worked up under reduced pressure so as to recover the organic promoter. After evaporation of the water, 160.5 g N,N-dimethylimidazolium iodide, corresponding to a yield of 99.7%, was obtained. N/I-analysis with 12.5 weight % N and 56.7 weight % iodine and IR-analysis indicated that the organic promoter salt recovered was very pure. The organic promoter salt was recycled into the reaction and the water distilled off was used again for extraction.
- 250 g catalyst solution cycled for methyl acetate carbonylation was taken from the catalyst cycle consisting of palladium carbonyl complex, tri-n-butylmethylphosphonium iodide as organic promoter, undistillable organic contaminants, acetic acid, acetic anhydride and ethylidene diacetate, and freed from distillable matter at a base temperature of up to 120° C. and under a reduced pressure of 2 millibars.
- the distillation residue was comminuted and introduced with agitation into 5000 ml water at 20° C. After 30 minutes, the suspension was heated to 65° C. while agitation was continued. After altogether 1.5 h, the residue was filtered, after-washed with water and dried at 120° C. under 2 millibars. 18 g weighed material which contained 0.846 g palladium was obtained.
- the water phase originating from the filtration was worked up under reduced pressure to recover the organic promoter. After evaporation of the water, 151 g tri-n-butylmethylphosphonium iodide, corresponding to a yield of 99.3%, was obtained. The organic promoter salt was recycled to the carbonylation reaction and the water distilled off was used again for extraction.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Inorganic Chemistry (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Carbon And Carbon Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3134348 | 1981-08-31 | ||
DE19813134348 DE3134348A1 (de) | 1981-08-31 | 1981-08-31 | Verfahren zur reinigung und rueckgewinnung der bei der carbonylierung von methylacetat und/oder dimethylether anfallenden, verunreinigten katalysatorloesung |
Publications (1)
Publication Number | Publication Date |
---|---|
US4440570A true US4440570A (en) | 1984-04-03 |
Family
ID=6140498
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US06/402,961 Expired - Lifetime US4440570A (en) | 1981-08-31 | 1982-07-29 | Process for purifying and recovering contaminated catalyst solution obtained in the carbonylation of methyl acetate and/or dimethylether |
Country Status (10)
Country | Link |
---|---|
US (1) | US4440570A (de) |
EP (1) | EP0073341B1 (de) |
JP (1) | JPS5845742A (de) |
AT (1) | ATE19004T1 (de) |
AU (1) | AU548509B2 (de) |
BR (1) | BR8205074A (de) |
CA (1) | CA1173020A (de) |
DE (2) | DE3134348A1 (de) |
MX (1) | MX161293A (de) |
ZA (1) | ZA826307B (de) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4557760A (en) * | 1983-06-08 | 1985-12-10 | Hoechst Aktiengesellschaft | Process for recovering noble metals belonging to group VIII of the Periodic System of the elements from a contaminated catalyst solution originating from the carbonylation of methyl acetate and/or dimethylether |
US4605541A (en) * | 1985-08-26 | 1986-08-12 | The Halcon Sd Group, Inc. | Recovery of noble metal values from carbonylation residues using immiscible liquids |
US4629711A (en) * | 1985-04-29 | 1986-12-16 | Hoechst Aktiengesellschaft | Process for purifying and recovering contaminated catalyst solution obtained in the carbonylation of methyl acetate and/or dimethylether |
US4650649A (en) * | 1986-01-21 | 1987-03-17 | Eastman Kodak Company | Catalyst recovery process |
US4659682A (en) * | 1985-07-08 | 1987-04-21 | The Halcon Sd Group, Inc. | Recovery of noble metal values from carbonylation residues |
US4985383A (en) * | 1989-02-10 | 1991-01-15 | Hoechst Aktiengesellschaft | Process for removing metallic corrosion products from a contaminated catalyst solution produced on carbonylation of methanol and/or methyl acetate and/or dimethyl ether |
US5047377A (en) * | 1989-01-28 | 1991-09-10 | Hoechst Aktiengesellschaft | Process for the purification and recovery of the contaminated solution of the catalyst produced on carbonylation of methanol and/or methyl acetate and/or dimethyl ether |
US20070142674A1 (en) * | 2002-12-23 | 2007-06-21 | Kanel Jeffrey S | Process for the recovery of phosphorus and iodine containing catalyst components |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1557924A (en) * | 1976-02-05 | 1979-12-19 | Western Electric Co | Irradiation apparatus and methods |
CA1338673C (en) * | 1988-04-15 | 1996-10-22 | Graham N. Mott | Catalyst recycle in the carbonylation of isobutylphenylethanol to ibuprofen |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2839580A (en) * | 1956-01-11 | 1958-06-17 | Exxon Research Engineering Co | Preparation of diethyl ketone |
US3821311A (en) * | 1970-05-21 | 1974-06-28 | Celanese Corp | Production of aldehydes from olefins |
US4013584A (en) * | 1975-05-27 | 1977-03-22 | Texaco Inc. | Processes for regenerating dispersions of ligand-stabilized, palladium and platinum (II) halide complexes used in carbonylation and hydroformylation catalysis |
US4287089A (en) * | 1980-03-20 | 1981-09-01 | Conoco, Inc. | Method for removal of water from activated carbon |
US4333884A (en) * | 1979-10-02 | 1982-06-08 | Hoechst Aktiengesellschaft | Production of acetic anhydride |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2790007A (en) * | 1954-11-19 | 1957-04-23 | Jefferson Chem Co Inc | Decobalting of aldehydes in the oxo process |
US3896047A (en) * | 1973-06-06 | 1975-07-22 | Gen Electric | Process for recycling a cobalt hydroformylation catalyst |
-
1981
- 1981-08-31 DE DE19813134348 patent/DE3134348A1/de not_active Withdrawn
-
1982
- 1982-07-24 EP EP82106711A patent/EP0073341B1/de not_active Expired
- 1982-07-24 AT AT82106711T patent/ATE19004T1/de not_active IP Right Cessation
- 1982-07-24 DE DE8282106711T patent/DE3270403D1/de not_active Expired
- 1982-07-29 US US06/402,961 patent/US4440570A/en not_active Expired - Lifetime
- 1982-08-26 CA CA000410225A patent/CA1173020A/en not_active Expired
- 1982-08-30 ZA ZA826307A patent/ZA826307B/xx unknown
- 1982-08-30 BR BR8205074A patent/BR8205074A/pt not_active IP Right Cessation
- 1982-08-30 AU AU87823/82A patent/AU548509B2/en not_active Ceased
- 1982-08-30 MX MX194209A patent/MX161293A/es unknown
- 1982-08-31 JP JP57150173A patent/JPS5845742A/ja active Granted
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2839580A (en) * | 1956-01-11 | 1958-06-17 | Exxon Research Engineering Co | Preparation of diethyl ketone |
US3821311A (en) * | 1970-05-21 | 1974-06-28 | Celanese Corp | Production of aldehydes from olefins |
US4013584A (en) * | 1975-05-27 | 1977-03-22 | Texaco Inc. | Processes for regenerating dispersions of ligand-stabilized, palladium and platinum (II) halide complexes used in carbonylation and hydroformylation catalysis |
US4333884A (en) * | 1979-10-02 | 1982-06-08 | Hoechst Aktiengesellschaft | Production of acetic anhydride |
US4287089A (en) * | 1980-03-20 | 1981-09-01 | Conoco, Inc. | Method for removal of water from activated carbon |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4557760A (en) * | 1983-06-08 | 1985-12-10 | Hoechst Aktiengesellschaft | Process for recovering noble metals belonging to group VIII of the Periodic System of the elements from a contaminated catalyst solution originating from the carbonylation of methyl acetate and/or dimethylether |
US4629711A (en) * | 1985-04-29 | 1986-12-16 | Hoechst Aktiengesellschaft | Process for purifying and recovering contaminated catalyst solution obtained in the carbonylation of methyl acetate and/or dimethylether |
US4659682A (en) * | 1985-07-08 | 1987-04-21 | The Halcon Sd Group, Inc. | Recovery of noble metal values from carbonylation residues |
US4605541A (en) * | 1985-08-26 | 1986-08-12 | The Halcon Sd Group, Inc. | Recovery of noble metal values from carbonylation residues using immiscible liquids |
US4650649A (en) * | 1986-01-21 | 1987-03-17 | Eastman Kodak Company | Catalyst recovery process |
US5047377A (en) * | 1989-01-28 | 1991-09-10 | Hoechst Aktiengesellschaft | Process for the purification and recovery of the contaminated solution of the catalyst produced on carbonylation of methanol and/or methyl acetate and/or dimethyl ether |
US4985383A (en) * | 1989-02-10 | 1991-01-15 | Hoechst Aktiengesellschaft | Process for removing metallic corrosion products from a contaminated catalyst solution produced on carbonylation of methanol and/or methyl acetate and/or dimethyl ether |
US20070142674A1 (en) * | 2002-12-23 | 2007-06-21 | Kanel Jeffrey S | Process for the recovery of phosphorus and iodine containing catalyst components |
US7541499B2 (en) * | 2002-12-23 | 2009-06-02 | Eastman Chemical Company | Process for the recovery of phosphorus and iodine containing catalyst components |
Also Published As
Publication number | Publication date |
---|---|
DE3270403D1 (en) | 1986-05-15 |
JPS5845742A (ja) | 1983-03-17 |
AU548509B2 (en) | 1985-12-12 |
MX161293A (es) | 1990-08-31 |
EP0073341A2 (de) | 1983-03-09 |
DE3134348A1 (de) | 1983-03-10 |
ZA826307B (en) | 1983-07-27 |
AU8782382A (en) | 1983-03-10 |
EP0073341A3 (en) | 1984-06-13 |
CA1173020A (en) | 1984-08-21 |
ATE19004T1 (de) | 1986-04-15 |
JPH0237214B2 (de) | 1990-08-23 |
BR8205074A (pt) | 1983-08-09 |
EP0073341B1 (de) | 1986-04-09 |
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